


You're Not Sammy

by ChibiDargon



Category: Supernatural
Genre: Accountant Castiel (Supernatural), Breaking and Entering, Crimes & Criminals, Dean Winchester Loves Pie, Fluff, Lawyer Sam Winchester, M/M, Mechanic Dean Winchester, POV Castiel, POV Dean Winchester, Prank Wars, Thief Castiel
Language: English
Status: Completed
Published: 2018-12-01
Updated: 2018-12-01
Packaged: 2019-09-02 22:10:02
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,959
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16795711
Author URL: https://archiveofourown.org/users/ChibiDargon/pseuds/ChibiDargon
Summary: Castiel is the CEO of an Accounting Firm by day, and a thief with all the best intentions by night.  One day, upon entering the house of his mark, Sam Winchester, Castiel finds himself caught by Sam's older brother Dean.Dean is a mechanic who wants to get back at his brother for waking him up so early every morning. He resolves to steal the wedding rings from the safe is Sam's office. He finds something unexpected instead.





	You're Not Sammy

It was not a particularly interesting day for Castiel. He had been drinking ungodly amounts of alcohol with Balthazar for the better part of the morning before Balth finally brought up the proverbial elephant in the room.

“So, Cassie. Since when are you stealing from people?” 

Well. That was blunt.

“I know not of what you speak, Balthazar.” Castiel had always had an abnormally high alcohol tolerance which, of course, pissed Balth off even more.

“Of course not. So, that wasn’t a sketch of you I saw on the evening news the other night then, was it Cassie?” Fuck, where did they even get a sketch. He had been so careful about it. Perhaps he should lay low for awhile. Oblivious to his drinking-buddy-with-benefits’ inner turmoil, Balthazar continued, “I mean, I can’t believe you would keep this from me, I thought we were close!” He cried in apparent anguish.

“Balthazar, police sketches are not always accurate. You know that.”

“It was you Cassie.”

“How can you possibly know that?”

“I saw your blasted fake ID when I was going through your wallet to pay for the Chinese food the other day! So, Mr. Allen, why have you been holding out on me.” He demanded.

Castiel sighed, well, this was bound to happen eventually. Better Balthazar than Michael, he supposed.

“Fine, Balth. You’re not incorrect. So, what,” He paused and pondered what Balthazar might do with this information, “ are you going to turn me in?”

The blonde scoffed and sipped at his whisky with gusto, “Turn you in? This is brilliant Cassie! My dearest friend has a secret identity! I’m simply offended you didn’t tell me, your bestest and only friend, that you live a life of crime.” He snickered at the last word. Cas couldn’t exactly blame Balthazar. He had been the very antithesis of a criminal his entire life.

He was Co-CEO of Novak and Novak Accounting. He had gone to school and graduated top of his class. He was arguably living in the “1%”. Hell, he hadn’t had even a parking infraction in his life. Castiel had it all. And yet, he had wanted _more_.

Well, not more exactly. 

But he hadn’t wanted to let himself forget who he was.

He’d been in High School when it happened. Watching some TV drama or another when for all intents and purposes, he should have been studying. Cas had been in his room, his brother Gabriel with him, eating candy and watching fucking TV. When someone had broken into their house, and killed both of their parents.

Gabriel and he we left with next to nothing, and had later resolved to do everything they could to help people who needed it. Who had lost everything. They become a modern version of Robin Hood. At first.

First pickpocketing. Then basic cons. They’d both learned to shoot when Cas started Senior year, however, neither of them particularly liked guns. Or violence. Castiel had, by some miracle, gotten a full ride to school for Accounting. Gabriel took their savings and joined him.

They left the life behind, or well. Gabriel did. Castiel had kept on going. Donating about half of what he earned, and stealing from those who didn’t need it. Who were already wealthy, and giving that money to people who were struggling to make it to the next day alive. 

Sure, he was rich, but he didn’t let it change him. Except his drinking habits. He had a lot better whisky now.

“Well I thank you for that Balthazar. Unfortunately, I need to catch a few hours of sleep before…” He paused, “work.” Cas winked and left Balth’s apartment, ignoring the cries of his friend to “Stay Cassie!” “Tell me more!” “Use protection!”, and called himself a cab.

  
Later that Day, at the Residence of one Samuel Winchester  


It was with a pounding headache and many regrets that Castiel got out of his cab and slid around the back of the house.

Castiel had been casing this target for the last month, and by now knew that Sam Winchester:

Was born May 2nd.

Was a Lawyer at a well respected firm an hour and 10 minutes away from his house by car in moderate traffic.

Was unmarried, but engaged to and living with another Lawyer, named Jessica Moore, who worked with Sam.

Woke up every morning at 5:45, jogged until 6:30, showered, ate breakfast, made a phone call (about 20 min in length on average) to his older brother, and left the house at 7:30 to arrive comfortably on time for work.

Had one sibling (at the very least one who he was in contact with), Dean Winchester. A mechanic who lived in the city.

Had no major security system.

Was extremely wealthy. In part because of his job and reputation, in part because of a shady business deal made with a man named Fergus ‘Crowley” Macleod, which left Sam with over $8, 000, 000. And a task to do… Something. Crowley had already been repaid, and that part of the deal was never Cas’s issue.

Returned home at 8:00 every evening like clockwork with Jessica.

And finally, was a genuinely good person, who did not necessarily deserve to be robbed, but he really had no need for 8 million dollars either. So, the previous point was moot.

Castiel picked the lock on the back door easily. He had three hours. He only needed twenty minutes.

After sliding through the door, Cas made his way to Sam’s office, where the man’s computer was. He retrieved a USB stick from his pocket, placing it into the open port on the side of the machine. Charlie needed twenty minutes to gain access to the account and drain 4 million of the shady money. The method she was using was apparently undetectable, so all he had to do was wait.

Castiel eventually got bored of doing nothing, and pulled up a game of solitaire on the computer. He was on his way to a victory when he heard the telltale sound of a key opening a lock.

_Fuck_

  
\---  


There was, in Dean’s humble opinion, something to be said for the wonders of sleeping in. Something Sam clearly disagreed with him on. As usual, Dean’s phone woke him at 7:00 am by blasting “Hedwig’s Theme”.

Dean answered, scowling at his little brother’s lack of respect for somebody needing sleep.

“What is it Sammy!” He yelled, burying his face in his pillow, and listening to Sam’s cackling on the other end of the phone line.

“Hey Dean! I didn’t wake you did I?” Dean’s devil of a brother asked all too innocently.

“No, no. No at all.” He grumbled. 

“Good, I would hate to interrupt Dean Winchester’s beauty sleep.” Dean could almost _hear_ Sam smirking.

“What do you want, bitch!?” He was awake now, there was nothing to be done about it. But if Dean had to endure wakefulness at this hour, he was damn sure gonna do it with coffee. Dean stood, and immediately regretted it. Right. He hung out with his friends Jack and Jose last night.

He stifled a pained groan as he stood. Sam was suddenly way to loud in his ear. And saying.. Something…

“...So Jess and I were wondering if you’d want to come to our place for dinner on saturday, I know you’ve got that thing you’re supposed to do but-”

“Sammy, I would be glad to go over to yours and eat some food, pie… pie. But I really can’t talk right now.”

“What are you, hung over?”

He paused, “Yes. Yes I am.”

“Alright. Talk to you later Jerk.” 

Dial Tone.

Dean spent the next hour or so making himself an extremely greasy breakfast and thinking about what he could possibly do to Sammy in retaliation for the freaking wake up calls every day. He had the day off so this would have to be a full effort.

By the time Dean had finished his extra crispy bacon, he had decided that the best way to get revenge on Sam was to really really fuck with him. He wouldn’t half ass this. 

Dean went to the store and purchased black gloves, black pants, a black henley and a black leather jacket. As an afterthought on the way out of the store, he also bought a black tuque. Nothing would freak Sammy out more than thinking somebody had stolen the rings, he decided.

After getting back home, Dean found himself falling asleep, typical. He had only slept for an hour or so. And made the executive decision to take a nice long nap before committing Breaking and Entering. And thievery, huh.

Dean set an alarm on his phone for four in the afternoon, he’d get a few hours of shut-eye. Then worry about what he’d say if Sammy was home when he got there.

BEEP BEEP BEEP

What was that noise?

BEEP BEEP BEEP

Why was it so close to his ear?

BEEP BEEP BEEP

Oh, right. An alarm clock.

BEEP BEEP B-

Dean got up and laughed out loud when he remembered that his plan for the evening consisted of breaking into his brother’s house and stealing the fucking wedding rings. Well, C’est La Vie. 

After he had dressed in all black, Dean made to get into the Impala, before realizing that the whole plan hinged on Sammy not knowing who had broken in. Scowling, Dean hailed a cab after stuffing his tuque into his pocket. Better people don’t suspect anything strange is happening.

So that is what found Dean contemplating picking his brother’s lock, before deciding that he may as well use the spare key (It was hidden under a small potted plant on the top step to the door. Anybody with half a brain would check there.) and walking, unannounced, into Sammy’s house.

  
\---  


There was still ten minutes left before Charlie was done hacking the computer. This absolutely sucked. Cas was about to be caught in the act of stealing 4 million dollars from a well respected goddamn lawyer because of course that was how he would be found out.

He dialed Charlie in the midst of his panic, and put the phone to the lowest possible volume. It probably wasn’t necessary, the other person in the house was making a lot of noise. Clearly, they were not aiming for subtle. The line connected just at the sound of glass shattering began.

“What’s up bitch!” Charlie said enthusiastically. Or, perhaps more accurately, shouted.

“Charlie. Someone is here.” Silence from the other side of the phone. Piano and loud singing from the living room.

“Aw shit. Ok, Cas. You’ll be ok. It’s not Sam Winchester. He’s still at work with Jess. I’ve got them on security footage right now,” Her tone had gone from playful to serious in a few seconds. “It’s probably someone _else_ breaking in. Just, try to stay out of sight. Don’t leave until they do.”

“Alright. Thanks, Charlie.” He hung up. 

Castiel made his way silently to the chair behind the desk. He picked it up, pulled it back, and climbed under the desk. Unless someone came into this room, and looked at the desk from behind. He was safe.

Minutes went by, hours. And the apparent chaos in the house died down. It was silent and Cas jumped when, just outside of the office, probably in the dining room, there was a cacophony of sound. A crash, a pained cry, and a string of curses and exclamations that would make _Gabriel_ blush.

The thing that startled Cas wasn’t any of those things though. What got him was the voice of the stranger. Because not only was it low, and rough and soothing, but he also recognized this as the voice of Sam Winchester’s brother. 

Well, fuck.

The man, Dean apparently, was getting closer. His entrance to the office announced by the creak of a floorboard in front of the door. 

_Don’t come over here, don’t come over here don’t come-_

_Fuck_

Dean was standing behind the desk, facing away from it, thankfully, at. The safe. Castiel had seen it earlier, was Dean actually stealing from his brother? He didn’t even know that man, but that didn’t seem like something he was capable of. Far as Cas knew, everything Dean had done until Sam was out of Stanford was for his little brother.

This must be some kind of mistake.

There was a _Beep_ as the pin to the safe was verified, and Dean chuckled.

Dean muttered “What the fuck am I even doin’ here” so quietly that Cas could barely make out the words. Before he could even try to understand what it meant, though, Dean started full body laughing.

And Cas was a professional. A professional Accountant. A professional Thief. A professional fucking liar, known for having an unbeatable poker face, and listening to Dean Winchester’s warm laughter was enough to make him crack.

There was something very wrong about that but Castiel didn’t have long to think on what it was before the laughter stopped, the chair was ripped away, and he was being held up by the lapels of his trenchcoat if front of an irate Dean Winchester.

  
\---  


What the actual fuck was going on here. Dean had broken in, smashed some dishes, played some Zeppelin, and stolen some rings. With his mission accomplished, and bleeding leg forgotten, he had started to laugh. And then someone else started laughing.

It only took him a moment to realize he wasn’t actually alone in his brother’s house. But that he must have _interrupted someone else’s crime_ because of course he did. Because of course this was his life.

Faster than he thought was possible, Dean had thrust the desk chair aside and grabbed the no-longer-laughing man by the lapels of his coat. 

“You’re not Sammy” Dean growled.

“Well, shit.” The guy said, monotone. “This is. Awkward.”

It took Dean a moment to collect himself enough to respond. The light in the flooding into the darkened room from the hall was enough that he could see the stranger. He had dark hair that… Quite honestly it looked like he’d just had sex. And when the guy looked at up at him to speak, in a voice that quite frankly, went further south than was entire appropriate in this situation, Dean got lost in the bluest blue he had ever seen. This man’s eyes looked like a million different shades of the color, expanses of oceans, all trapped in a world of its own. Dean thought that if he didn’t look away quickly, he ran the risk of never being able to.

After a while of neither man looking away or speaking, Dean realized that he had been looking into this random dude’s eyes for _far_ longer than was socially acceptable. And, with no small amount of difficulty, looked away.

“What the fuck are you doing here!” Dean demanded. 

The man with eyes like oceans responded calmly, “I am stealing a sum of money from your younger brother.”

“You know who I am.” It wasn’t a question.

“Dean Winchester.” The thief said.

“Alright, you’ve got me at a disadvantage here. Who’re you?” At that the man smirked. He seemed to radiate mischief for a moment before he schooled his featured.

“Emmanuel Allen.” He answered smoothly. It was a bald faced lie. Dean could tell.

“Uh huh,” He sighed. Just as Dean opened his mouth to continue, Emmanuel cut him off.

“You know why I am here now. Why are you here. At first I assumed that you were inebriated, but clearly you are not. I am not the only one who came here to steal something this evening.” The man had tilted his head and drawn his eyebrows together. In a way that radiated a frankly adorable amount of genuine curiosity. _Adorable? Really Winchester? Get it together_

“It’s a prank. I’m stealing his wedding rings” Dean responded truthfully before he could think better of it. 

“That does not seem like a very entertaining prank.” Emmanuel deadpanned. 

“Not for Sammy,” Dean admitted, letting go of Emmanuel’s coat and righting the chair before sitting in it. “But hilarious for me. He’ll think they’re gone, and I’ll tell him I had them the whole time. If it goes as planned, he’ll never even know I took em’.” He explained.

Emmanuel regarded him for a moment before asking “What about the state of the house?”

Dean shrugged. “Eh, he’ll think whoever really robbed him tonight,” he pointed at the other man, “did it.”

  
\---  


Well, wasn’t this an interesting turn of events. Dean seemed to know that ‘Emmanuel Allen’ was an alias but let it go easily. Perhaps he could get some answers about the transaction that had brought him there.

“Dean, do you know Fergus Macleod?” Dean blanched, and Castiel’s curiosity was officially piqued.

“Yea. I know Crowley. Don’t make deals with that fucker. They bite you in the ass.” Huh, that was a curious response.

Castiel considered his options. Regardless of what he did, he’d likely end up in prison, so. He may as well get some answers first. 

“I…” Dean turned to him, but how was he supposed to explain this? “I am here because your brother has an excess of money which he got in a deal with Crowley 8 years ago. I’ve no idea what the payment was, but I am in the business of taking money that will just sit around collecting dust and interest and putting it to use with those who need it.” Dean raised an eyebrow when he paused as if to say ‘go on’.

“An associate of mine had hacked the account remotely and transferred $4 million of the dirty money to be filtered through other sources in small amounts and distributed clean in about a month to charities and individuals alike.”

“Why the fuck would you tell me that?” Dean breathed.

“I see next to no ways this night ends without me being arrested. I can rest easier with answers. I have been wondering about Crowley and the other side of the deal since I found out about it last month. Do you know what Sam paid for the money?”

Dean chuckled a humorless laugh, “Yeah, although that’s not exactly how it happened.” Cas tilted his head in confusion. “8 years ago, Sammy is approached by this guy right? He says his name’s Crowley. And he wants Sam’s help with something. He tells Sam to approach this guy, Lucifer, in a bar and take him home that night. If he does it, it’ll be worth it for Sam. If not, he’ll kill Sam,” Dean snapped his fingers “Jess,” _snap_ “and me.” _snap_. “Sam agreed. He took the guy home and when he got there, Lucifer was drunk enough that he didn’t see Crowley in the apartment in time. He shot him dead, and paid Sammy off.”

When Castiel didn’t reply Dean took it as a cue to continue.

“Course, Sam never touched the cash. It was dirty and it made him feel guilty. He wanted to get rid of it, but there really wasn’t a way y’know? So I me-” Dean was interrupted by the unlocked door opening and a two seperate high pitched screams.

“It would appear your brother has arrived. I would appreciate it if you would dissuade him from calling 911.” Castiel said calmly and quietly. Dean chuckled at the delivery of the comment as he stood.

“Sammy!” Dean called. He gestured for Castiel to follow him.

This certainly was an interesting turn of events. 

A tall man with long hair who Castiel recognized as Sam, met them in the living room.

“Dude what the hell are you doing here!?” Sam’s expression faltered for a moment, “Dean did you do this!” He exclaimed, pointedly looking at the shattered glassware.

“Ummm” Dean said eloquently, “You’ve been pranked?” he continued, looking distinctly guilty.

“What the hell Dean, you broke into my house while I was at work and trashed the place? That’s not a prank dude, that’s a crime. It’s not funny.”

“I concur.” Cas said. Drawing, for the first time, the attentions of Sam and Jess. The former started, eyes widening comically in shock and confusion, the latter sighing and expressing her desire to go to sleep “right the fuck now” and leaving in the direction of the bedroom.

“Somebody start talking. Now.” Sam said, exasperated.

Dean was looking down at his feet in shame and Castiel saw it as his opening to voice a request and some personal confusion. After he explained what had happened. Which proved to be a very short explanation.

“I came to steal a sum of $4 million dollars of what was paid to you by a man named Crowley. Whilst I was in your office, I heard your brother enter the house. For approximately two hours he wreaked havoc on the common areas of the house, before entering the office, where he found me hiding beneath the desk. We discussed our respective reasons for being here and were interrupted by your entry to the house.” Castiel took a breath and before Sam had a chance to formulate a response, he continued.

“Sam, I know about your dealings with Crowley, and I would like to ask for your permission to redistribute the remainder of the it along with the $4 million I already took to various charities and persons internationally rather than simply leave it. My associate and I have ways to validate the money. It would never be traced back to you.”

Nobody spoke for a moment. After what seemed like an eternity, Sam’s shoulders bled out the tension that had gathered up when he had been shouting at Dean.

“Sure. I. Yeah?” He shrugged “I never wanted it anyways and if you can do some good with it…” He shrugged again, awkwardly.

Cas nodded, and Dean returned to where he had been standing but had apparently vacated at some point with a plate of pie and began eating it.

Simultaneously Cas and Sam started hysterically laughing. It took about ten minutes for them to get ahold of themselves, bothe were literally on the floor and they hurt from laughing too hard. When he could speak again Sam peered at Castiel and asked “Aren’t you Castiel Novak?”

Which of course set them off again.

  
An hour or so Later  


Castiel had called Charlie and the rest of the money had been transferred seamlessly. Dean and Cas were talking on the porch about the most important things alone, as Sam had elected to go to bed.

“Dean, I don’t care how many times you tell me to watch it. I will not be attending a showing of the original Star Wars trilogy alone.” Castiel repeated for what felt like the hundredth time.

“Does that mean you’d go if I went with?” Dean asked, clearly failing miserably at going for casual, and Castiel didn’t miss how his gaze lingered on his lips for a moment too long.

“Only if you bought me dinner first.” Cas said seriously.

Dean gazed at him for a moment before asking, “Why, Cas, are you asking me on a date?”

Cas smirked. “If you’d be amenable.”

Meeting his eyes full on, Dean replied easily, “I’d be honored.”

That Friday Dean and Castiel watched the original Star Wars Trilogy. 

That Saturday Charlie, Dean and Castiel worked together to get Crowley arrested. Hilariously on Grand Larceny.

That Sunday Balthazar, Dean, Castiel, Sam, Jess and Gabriel had a party to celebrate.

Dean offered to become a member of Castiel’s crew the next Monday, and Castiel accepted, enthusiastically. Twenty minutes later, Castiel and Dean successfully traumatized Sam.

And all was well.

  
THE END  


**Author's Note:**

> Side note, I didn't exactly know how to work this in to the end. Dean gives the rings to Sam just before Sam goes to bed without a word, and then Sam tells him that he's going to call the caterers for the wedding and tell them not to bother with the pie table. 
> 
> Dean gets progerssively more desperate in his pleas for pie. Sam finally laughs and tells him "Don't worry jerk, that's too cruel, even for me."


End file.
